홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

4-Methylmorpholine → N-[N-Phthalimido-3-(2-thienyl)-L-alanyl]-6-hydroxy-L-norleucine, methy ester

HRID 1683343
노트
인쇄 미리보기

반응식

HRID 1683343 반응식
CN1CCOCC1.Cl.[OH:9][CH2:10][CH2:11][CH2:12][CH2:13][C@@H:14]([C:16]([O:18][CH3:19])=[O:17])[NH2:15].[C:20]1(=[O:41])[N:24]([NH:25][C@H:26]([C:33](O)=[O:34])[CH2:27][C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)[C:23](=[O:36])[C:22]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:21]12.OC1C2N=NNC=2C=CC=1.C(N=C=NCCCN(C)C)C>C(Cl)Cl.CN(C)C=O>[C:23]1(=[O:36])[N:24]([NH:25][C@H:26]([C:33]([NH:15][C@H:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][CH2:11][CH2:10][OH:9])=[O:34])[CH2:27][C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)[C:20](=[O:41])[C:21]2=[CH:40][CH:39]=[CH:38][CH:37]=[C:22]12
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 11680005methyl (2S)-2-amino-6-hydroxyhexanoate hydrochlorideHCID 70051103HCID 70051103, 화합물HCID 178418300HCID 178418300, 화합물

생성물 1

HCID 131719431N-[N-Phthalimido-3-(2-thienyl)-L-alanyl]-6-hydroxy-L-norleucine, methy ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

N-Methylmorpholine (1.51 ml., 14.5 mmol.) was added to a solution of 6-hydroxy-L-norleucine, methyl ester, hydrochloride (8.53 mmol.) in methylene chloride (34 ml)/dimethylformamide (9 ml.) at room temperature under argon. The resulting mixture was cooled to 0° C. and N-phthalimido-3-(2-thienyl)-L-alanine (2.57 g., 8.54 mmol.), hydroxybenzotriazole (1.19 g., 8.80 mmol.) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (1.80 g., 9.4 mmol.) were added sequentially. After stirring at 0° C. for 30 minutes, the mixture was warmed to room temperature and stirred for 1.5 hours. The volatiles were evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was washed successively with 0.5 N hydrochloric acid, water, saturated sodium bicarbonate, and brine, and the organic layer was dried (sodium sulfate), filtered, and concentrated. The residue was flash chromatographed (Merck silica gel) eluting with 2:1 ethyl acetate/hexane to give 3.13 g. of title compound as a white foam. TLC (5% acetic acid in ethyl acetate) Rf =0.68.

후처리

  1. temperaturethe mixture was warmed to room temperature
  2. stirringstirred for 1.5 hours
  3. customThe volatiles were evaporated
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed successively with 0.5 N hydrochloric acid, water, saturated sodium bicarbonate, and brine
  6. dry with materialthe organic layer was dried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed (Merck silica gel)
  10. washeluting with 2:1 ethyl acetate/hexane
  11. customto give 3.13 g

출처 및 근거

ORD 기록
ord-075c8a8bd0d2438a82bc6f2098a3aa84
출처 데이터셋
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05637698

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트